Filter Multi-Select column based on Select Control

I have a table base on seasons and years, I want to filter for a year’s (12 months) work of data based on a select control.

For example:

Select Control = Winter 378 – the view should show data for Winter 378, Autumn 378, Summer 378, Spring 378

Or

Select Control = Summer 378 – the view should show data for Sumer 378, Spring 378, Winter 377, Autumn 377

To achieve this I’ve created a calendar table for each of the year/seasons and created a multi-select column (Calendar Range) where I’ve defined which Select Control (Header Date) results should result in that season/year being filtered.
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I have tried:

Calendar Range.filter(Header Date)

Header Date.in (Calendar Range)

Calendar Range.in (Header Date)

Calendar Range.contains(Header Date)

And no results are found

What am I missing?

Thanks guys